Trifluoroacetic acid → HCID 12969041, compound

HRID 991768Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:43]=[CH:42][C:12]([O:13][CH2:14][C@@H:15]([OH:41])[CH2:16][N:17]([CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([NH:33][CH:34]3[S:38][C:37](=[O:39])[NH:36][C:35]3=[O:40])=[CH:29][CH:28]=2)C(=O)OC(C)(C)C)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:13][CH2:14][C@@H:15]([OH:41])[CH2:16][NH:17][CH2:25][CH2:26][C:27]2[CH:28]=[CH:29][C:30]([NH:33][CH:34]3[S:38][C:37](=[O:39])[NH:36][C:35]3=[O:40])=[CH:31][CH:32]=2)=[CH:42][CH:43]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 86584667HCID 86584667, compound

Product 1

HCID 12969041HCID 12969041, compoundYield 58%

Procedure

This compound was prepared from tert-butyl (2 S)-3-[4-(benzyloxy)phenoxy]-2-hydroxypropyl{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)amino]phenethyl}carbamate and trifluoroacetic acid in substantially the same manner as described in example 1, step e, with one modification, the product was isolated as the free base and recrystallized from methanol, tetrahydrofuran, hexanes to give a yellow foam solid (58% yield): mp 152° C.; MS m/e 508 (M+H)+; 1H NMR (DMSO-d6 300 MHz) δ2.68 (m, 2 H), 2.81 (m, 1 H), 2.88 (m, 4 H), 3.85 (m, 2 H), 4.00 (m, 1 H), 5.02 (s, 2 H), 5.45 (br, 1 H), 5.99 (d, 1 H), 6.59 (d, 2 H), 6.66 (d, 1 H), 6.84 (d, 2 H), 6.86 ( m, 2 H) 6.92 (m, 2 H), 7.28 (m, 5 H), 8.80 (br, 1 H);

Workup

customthe product was isolated as the free base
customrecrystallized from methanol, tetrahydrofuran, hexanes

Sources & evidence

ORD record: ord-af4c5111badf43858bb2bfd4b3dad153
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06465501B2

Reaction notes

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